Monday, February 24, 2014

I used to visit a dominatrix who was a lot of fun. She was
not a pain freak, and she respected limits. The reason I came back to her is
because she understood the sissy shame I needed to get into.

This particular visit, I brought my three suction cup
dildos. The first is obscenely large, probably as long as my forearm. It’s
certainly not something to be taken anally, but its sheer size would make any
sissy feel quite diminutive. I can barely get my lips around it. The second was
a 10” model, and the third was about 8” and has a squirting feature. The bulb,
which held about a half-cup of fluid was on the end of a length of tubing, and
I filled it with a milk mixture. It wasn’t as thick as real cum, but it would
do the trick. Mistress would take the dildos and stick them to the mirrored
wall at about crotch height. They were added to the two she already had placed
there. So there were five large dicks waiting. We would be back to visit them
later.

Our typical session usually began with a spanking. Then
she would dress me up in sissy underwear, stockings, clothes and high heels and
give me another spanking for getting turned on by wearing women’s underwear. As
I would get more whiney, she would find it necessary to “install” a butt plug, which
was preceded by a probing examination with medical gloves. My pussy bottom would
get a thorough lubing and inspection with one, then two, then three fingers before
the plug was easily pushed deeply inside. She had me put on a thong girdle
which would hold the plug firmly in place and keep my bottom exposed for more discipline.

She would then strap a cock gag around my face to keep me
quiet and administer an even stronger spanking with a paddle. I would become
progressively more docile with each step. I winced and whined and cried for
help while she admonished me for being a sissy.

Mistress would be wearing a strapon under her short skirt
and the end would hang slightly below the hemline. After the spanking on the
couch, she ordered me to kneel at her feet. She spread her legs exposing her
cock nestled between her pantyhose covered thighs and announce, “I want some
head!” I feigned disgust and refused. I was back over her lap in short order
receiving an even harder ass slapping as I pleaded with her to stop. She only
relented after I repeatedly begged her to let me suck her cock. Then I was on
my knees enthusiastically sucking her big cock.

She had me stand up, and she led me over to the mirrored
wall. “I invited some of the neighborhood boys over. They want you to come out
and play,” she said, pointing at the five big cocks stuck to the wall. I tried
to hide behind her like a scared girl.

“Make them go away,” I pouted, “They just want blowjobs!”
I pointed at the squirting dildo and said, “And that one boy lies! He says he
won’t come in your mouth, and then he holds my head and shoots his nasty spunk
down my throat. He’s disgusting!”

Mistress corrected me, “Now Missy, they’ve come to visit,
and you should entertain your visitors.” She pushed me to my knees in front of
the group of boys. She coaxed me over to the largest cock. “Show him you’re glad
he came to visit.” She pushed my head toward the massive cock as I dutifully stroked
it and kissed it. So embarrassing.

She lifted up end of the huge cock and said, “Kiss his
balls, Missy. Lick them. Suck his balls. They have a lot of jizz in them.”

I was trying to work on the one cock while she had my
jacking off two of the other five boys’ dicks. She had me move from one to the
other while she directed me to kiss and suck their balls, lick the underside of
their dick heads, and bob up an

d down on them.

“They all want you to blow them!” she laughed. She would roughly
push and pull my head on them.

At one point, she told me to open my eyes and see myself
in the mirror. “Look at the cocksucker!” she said. “That slut is sucking off
five boys! What a whore!”

I sucked the dildos for at least 20 minutes. She made me
work hard, and my jaws were aching. From one, to another, and back again to
another. Finally she directed me to the last one, the squirter. I resisted, “Please.
NO!” I pouted, “this boy lies! He says he won’t cum in my mouth, and then he
shoots it down my throat or all over my face. It’s gross!”

Mistress said in a reassuring tone, “He said he won’t.
You have to give him what you gave his friends. Just suck it a little bit for
him.”

She pushed me onto the head of his cock while she reached
for the squirt bulb. She had me lick the
underside of his cock and suck his balls. As my lips reached the end of his
dick, she pushed my head onto it very aggressively.

“Oooh, he’s getting impatient, Missy! Suck him real good.”
She gently squeezed some “precum” out the end of the dildo, and I recoiled. I
looked up at the imaginary boy, and warned him, “Don’t you dare cum in my
mouth!”

Mistress had me sliding his cock in and out of my mouth
rapidly. I was almost in a frenzy. She got close to me and whispered, “You LOVE
cock in your mouth, don’t you, bitch? You love the feel of it. You love the
taste of it. You’re a cocksucker and you can’t stop!”

I worked up the speed until I thought I’d pass out. Then suddenly
she grabbed the back of my head and pushed it down hard on the cock until it
was pushing on the back of my throat and I was choking on it. With that, she
gave the bulb a hard squeeze, and a huge load of “cum” hit the back of my
throat. I coughed and pulled away just as another shot hit me in the face. She
laughed at me as I reacted with disgust to my face being drenched.

“Don’t stop!” she ordered, “Finish the job!” I stroked
his cock, and another load of jizz hit me in the face. She laughed as she
pushed my mouth back on it, and another load spewed into my mouth. Keep in
mind, the bulb holds about 20 times more than an average man would cum. I had
been given several loads down my throat, and it was all over my face and hands.

Mistress just laughed, and then she instructed me to
clean him up. She ordered me to lick the length of his dick, lick and suck his
balls, and bob up and down on the cock several more times. I stroked out even
more “jizz” and licked the end of his cockhead. I was exhausted.

“Look at yourself!” Mistress pointed to me in the mirror
and chided me. “You look like a shameless tramp! This is how a girl like you
gets a reputation, sucking off five boys in the back yard! No wonder they like
to come visit you. They know you’ll give them blowjobs. You’re nothing but a common
street whore!”

I felt like one.

Sessions with this dominatrix always concluded with me
eating my own cum, and I had taken it many different ways. The typical way was
to lick it off a dildo, but I’ve also had to cum into a glass, onto a cookie,
into a large serving spoon and into my hand before having to consume it. Sissies
have to eat cum.

This particular session, she brought me over to a frame
which looked like some kind of exercise machine that had been adapted. She brought
my legs and feet up high while I was masturbating. I’ve done this many times
before, usually on my own. This time, she stood over me jacking her strapon
cock with a wicked smile.

“Open your mouth. I want to see if I can hit the target,”
she directed. In this somewhat inverted position, I was wanking furiously while
she stroked her “cock,” smirking at my predicament. Then she started pushing on
the butt plug. That did it. I screamed while my own cum dripped into my mouth and
mostly onto my face.

She looked down over me and told me to lick my upper lip and
the corner of my mouth so I could taste more semen. I whimpered while she
laughed at my pathetic condition.

Before letting me get up, she berated me a little more
and instructed me to let the jizz dry on my face. I would be allowed to wash my
face after I had changed. It burned and felt gross while I changed clothes.

Wednesday, November 27, 2013

I did a scene with an escort girl one time. She dressed up in my pants and shirt. Underneath she wore a strapon harness with an ejaculating dildo filled with milk. We played a scene where I was the hot secretary in the office. I was wearing a very short dress with black pantyhose, a pushup bra and very high heeled pumps. One thing led to another, and she was forcing herself on me. She kept feeling me up while I tried to fend off her advances. At one point I slapped her on the face for being so forward and rude. I was acting like a prissy stuck-up girl.

She blamed me for being a cock tease in my short skirt and sexy legs. Eventually she forced me to my knees and told me I was going to suck her cock. I told her I wasn't "that" kind of girl, but she told me she was "that" kind of guy. She put my hand on her crotch and made me feel her 8" cock. I kept trying to get away, but she forced me into the corner. She unzipped her pants and pulled out her cock. I kept trying to resist but she didn't give any choice, and like a frail little thing, I was afraid of being hurt so I did as I was told.

She pushed her cock against my lips. "Suck my cock, baby. Do it!" I shyly put it in my mouth, and she grabbed the back of my head and impatiently started fucking my mouth. I gagged and tried to get away, but I was helpless. I pulled it out long enough to demand she not cum in my mouth because I was a good girl. She said, "Don't worry, baby, just suck it." She shoved it back in my mouth.

I started stroking her big cock and sucked it like a scared little whore. She kept telling me what a good cocksucker I was. I kept stopping to tell her not to cum in my mouth. The whole time, of course, she had the sqeeze bulb for the squirting dildo in her hand. She sat on the bed as I knelt in front of her and serviced her big cock.

Several times I could taste the "precum" (milk) coming out the tip of her cock, and I told her again not to cum in my mouth. I was a good girl and didn't do that. She was a great actress and started thrusting her hips as her breath quickened. As she was about to "cum," she again grabbed the back of my head. I could feel the first spurt come out the head of her cock and hit the back of my throat, and I backed away in disgust. She held my head while she shot the rest of her load on my face. The bulb was pretty good sized, and she shot wave after wave of white cum on my face while I reacted in disgust.

I felt so used and dirty and cheap with all her jizz on my face. She told me my boyfriend should be proud of me for being such a good cocksucker.

For the finale, she had my jack off and cum all over the dildo. Then she had me get back on my knees and told me to clean her cock real good. I obediently licked up all her (my) jizz from the cock while she told me to swallow her cum.

After I finished cleaning all the cum of her cock, she put her hands on my face and sweetly said, "That's what you get for being a prick tease, bitch." She laughed at me and made me feel like a degraded girl. She put her cock back in her pants and left me on the floor like I was going to cry.

That was a really hot scene. I've played it over in my head many times.

Wednesday, June 22, 2011

In my post below "Have you ever worn women's silky underwear?" Chrisissy replied that maybe telling them might be more fun than just ending the relationship. Well, Chrisissy, you're right, and I have ended a couple relationships that way.

In fact, I went through a phase with a number of women where I would drop the hints, and when the reactions were largely unfavorable, I'd just bail via wearing something obviously feminine. In most cases, these women didn't know other people in my sphere. One of my favorite "drops" would be about tights. I'd be talking about working out and wearing my tights. It's almost funny how the reactions of about three different women were almost identical. They'd simply reply, "Tights?" In every case, they said it in two syllables, "tie-eets" with a rising inflection.

"Sure. I wear them sometimes when I'm on my elliptical machine." Their reactions would be guarded. I'd act like it was normal. After all, lots of guys wear tights for working out.

One girl was inquisitive and pressed, "What kind of tights?" I acted dumb. "I dunno. Danskin, I think."

"You mean footed tights?"

"Well, I guess. Aren't they all footed?"

"Ummm... oooo-kaaaay." I was starting to open the door that she would eventually close quietly yet firmly. I didn't care at that point.

Sometimes I'd get a little frisky knowing the end was near. I showed up to meet a date at a restaurant wearing Chic jeans and a plain woman's blouse. At a distance, it looked quite normal, but it didn't take her too long to notice the nature of my outfit. She never returned my calls again.

Another girl surely spotted the waistband of my pantyhose before never speaking to me again.

A girl named Lois was cautiously OK with my tights. I stopped by one day after a trip to Target where I had bought a leotard. A thong leotard no less. I told her I had bought this top but thought I might have to take it back. I showed her the top part of it without letting her see the cut of the bottom. "That's a ladies top..." she reported. "Well, it's a fairly plain design. Let me try it on."

In the bathroom, I said, "Oh goodness!" acting surprised.

"What is it?" she inquired.

"Do you know what a thong is?" I said, embarrassed.

"Yes..." in a two-syllable tone.

"I don't believe this..." opening the door to reveal my black tights and thong leotard. "I guess this will have to go back."

Poor Lois was half laughing but alarmed that I'd buy let alone wear such a garment.

Oddly enough, that afternoon Lois gave me two pairs of her panties before sending me out. She never returned my calls again. I can still hear her reaction to my leotard and tights.

Thursday, June 9, 2011

Put your elbows on the table, Sissy. That's it. Just relax, now. I'll be very gentle. Let's just unzip you back here... Now, honey, just relax. It's only going to hurt for a short while. I'm going to use lots of lube on my strapon... and then I'm going to pene... trate... you... gently. Don't fight it. It will only hurt more. It's almost all the way in now. Don't cry...

Monday, October 18, 2010

"What?" I responded, curiously. This phone conversation had just taken a very rapid turn.

She repeated slowly with more insistence, "Have you ever worn women's silky underwear?"

Cindy was the original Miss Priss. Well educated, prim, proper, and fussy. We'd been dating for about six months, and I don't know what really attracted me to her.

As with many women I dated, I dropped hints here and there... like how I "had to" wear pantyhose under my pants to do some work outdoors on a particularly cold and windy day. Or how I dressed up as a girl for Halloween. If it got the right giggly response, I would tell them how my girlfriend at the time had dared me wear EVERYTHING including bra, panties, pantyhose, girdle, heels, etc. Well, OK, that's not entirely true because Terri, the girl I was living with, knew full well of my crossdressing, and she just helped me dress up one Halloween. She provided some of the outer wear, and I already had more lingerie than she did.

Most women would find it amusing and think of me as a more evolved man because "now you know what we have to go through," and I would engage them in an extended conversation about wearing such underthings and navigating in high heels and a girdle (I wouldn't mention that I particularly like girdles because they hold a butt plug firmly in place). Maybe I'd throw in a little tidbit about how I wore a silky nightgown to bed that night after the party. (OK, I wore a nightie to bed every night with Terri.) That might get a real rise because I would be hitting the edge of concern. One girlfriend giggled and said, "I'm beginning to wonder about you!" and then I'd back down and say, well, it was an interesting experiment.

Cindy wasn't amused by this, although she wasn't immediately repulsed. And while I didn't go so far as revealing the "nightie" night, I continued to bring up the subject gingerly until it must have reached critical mass for her. Perhaps she had a consultation with a female friend or her mother, expressing concern over these things that I mentioned. "Just ask him outright! Ask him if he ever wore women's silky underwear. After all, that's what 'those men' like to do!"

I was a bit bemused by the nature of her question. I toyed with retorting, "You're worried about 'silky underwear?' Women's cotton panty briefs don't count? What about pantyhose? I wear them almost daily. I have some bras that aren't silky per se. Are dresses, blouses and skirts OK?"

But I could tell that Miss Priss was launching an investigation here. She had to get to the bottom of this crossdressing issue, and she was intent on how I answered. I figured I'd stall for time and fall back on known issues.

"I told you I dressed up for Halloween..." I don't think I had told her about the extent of my underpinnings, but now I was essentially admitting to the dread "women's silky underwear."

"Yes you told me about that..." Her tone said she was demanding more. "What other times?"

"And I wore them the night before..."

"You did?" She was beginning to become alarmed.

"Yes, of course, we had to see if everything fit, so I had to try on all the underwear, too." Again another admission with "all the underwear." Let her imagine what that meant. As in, full blown lingerie. As in "WOMEN'S SILKY UNDERWEAR!!" She didn't quiz me about the details. I wished she had. I would have given her details about the lace underwire bra and the satin panties with the lace at the leg openings.

She remained on task, "Okay, other than that?"

"Well, I told you about wearing pantyhose. I guess you could say they were silky."

She quickly returned, "Other than those times, have you worn women's silky underwear?"

Time to bail. She isn't going to ever accept it in any way, shape or form.

Wednesday, September 22, 2010

Before much of what I've written about previously happened, I came out to two girls named Jill and Tracey. We were just friends and would pal around together, often going out to dance. Jill was a lesbian, not necessarily butch but she never really wore feminine clothes. Jill had the hots for Tracey. Tracey was very feminine, girly, and mostly straight although later she "dated" other girls. I came out to Jill first. By coming out, I'm referring to my crossdressing. I guess because she's gay I figured she would understand, and she did. We often went out for drinks, and we would notice the same women together. Over time, there were other aspects of my sissyness that I would reveal to her.

While we had become close friends, Tracey had no interest in me romantically. She was younger than me, and she had boys that she would date. We often talked, and she confided in me about them. I guess it was a form of cuckolding to hear about her dates. I tried to encourage her to give me all the details about what she did with her boyfriend. I secretly wanted her to tell me how he fucked her real good so I could know that I couldn't provide her with the satisfaction her boyfriends gave her.

Somewhere along the line, I told Tracey about my crossdressing, too. Jill was a bit of a gossip, and I figured she had told Tracey anyway. She was fine with it, and we'd often talk about clothes and things, just like two girlfriends. The three of us would often hang out at my place before or after dancing, and I'd often relax into something more comfortable. They both thought it was cute that I'd be wearing girls jeans. They knew I wore feminine underwear most all the time, and they'd see my pantyhose on my ankles or they'd see my bra through my shirt. It was fun to hang out with the girls. Sometimes they'd gently tease me about what I was wearing.

Jill was a bit of an instigator in trying to get things naughty and sexy. My theory is that Jill thought that if everybody got turned on, maybe she could get into Tracey's pants. I also found Tracey attractive, so it was a weird triangle.

Once, Tracey ordered a nightgown as a gift from one of my many lingerie catalogs. When it arrived at my place, Jill teased and suggested that maybe I should model it for them. Tracey agreed, and I went into my bedroom, put the nightie on over my pantyhose, walked shyly out into the living room and did a couple twirls for them. I was going to take it off right away, and they both encouraged me to leave it on for awhile. This was very arousing, wearing a silky full length nightgown and pantyhose in front of both of them. After some time, I was standing in kitchen talking to Tracey when Jill came up behind me and pulled up the nightie above my waist. Tracey stood there grinning while looking at my very hard dick encased in control top pantyhose. After about 20 seconds (seemed like an eternity), I acted embarrassed and pulled the nightie back down.

Over time, little teasing events like this eventually led up to one night in particular when Jill and Tracey asked me to put on a little lingerie show for them. "We want to see more of your collection," they said enthusiastically. It was almost as if they had schemed this. Since they had seen me in a nightie before, I put on one of my own and modeled it for them in the living room. “That’s OK, but let’s see something sexier!” My next trip out of the bedroom was more revealing. I have tons of stuff, so it could have been a very long night. Each time, they encouraged me to wear more and more revealing things for them. I thought I had reached their limit by wearing sheer panties, but they were trying to goad me into the full monty. So I finally came out wearing a bra, garters and stockings and my only pair of crotchless panties.

“That’s much better!,” they gleamed. I was actually embarrassed now, and I felt objectified as a woman would be exposed in front of group of men. They had me walk around for them, and whenever I tried to cover my dick, they told me to take my hand away. I was sticking straight out, and after a short while, I started to lose my hardon. “Don’t let it go soft!” Both of them were enjoying looking at my hard dick. I stroked it to get it hard again. “Yeah! We want a REAL show now!” I couldn’t believe this. I was standing in front of these two women wearing sissy clothes and rubbing myself.

One thing I learned rather quickly is that it is very difficult to maintain an erection in front of an audience. They were clearly enjoying the show, and they made it clear they wanted to see me masturbate in front of them. I felt embarrassed stroking fast as I normally would, and yet it felt so sexy to stand in front of them stroking while they grinned and watched.

I knelt on a stuffed chair and tried to concentrate on the feeling. Eventually, they turned their attention to a music video on the TV and gave me a bit of a break from the performance anxiety I was obviously exhibiting. I was relieved for the break but felt puny because I couldn't entertain them enough to keep their attention from the TV. I felt like the little boy wanking in the corner while the adult girls watched TV, ignoring me.

After what seemed like a very long time with them looking away, I finally got up to the edge, and started making noise like I was going to cum. They returned their attention to me. I’ll never forget the amused look on Tracey’s face as she turned her attention back to me smiling and watched as if I was an entertainer.

I started to get nasty. “I’m gonna fuckin’ cum!” Tracey grinned and coyly replied, “Yeah, fuckin’ cum.” I moaned and started to scream as I shot my wad. I felt as though I needed to show the goods, so I came proudly into my hand while they watched the puddle build. Both of them laughed as I shuddered and gave out that last sigh. They finally gave me a round of applause, and I must have turned bright red. The inevitable post-orgasm shame of wearing the clothes came over me, and I was in a hurry to run back to the bedroom and get more decent.

When I came back, they both told me it was great fun for them. I was still a bit embarrassed. Tracey asked, “You really like to masturbate wearing women’s underwear, don’t you?” I admitted I did. “You obviously enjoy it!” The rest of the night was light. They assured me they enjoyed the show and didn’t make me feel like a complete pervert.

Believe it or not, dear sissies, this really did happen. What may be even harder to believe is that there is a Part Two to this story. Sorry this has taken so long to write, but now that I’ve set the stage, hopefully I can write the second half a little quicker.